EP4163305B1 - Verwendung von poly-alpha-1,3-glucan-ethern als viskositätsmodifikatoren - Google Patents
Verwendung von poly-alpha-1,3-glucan-ethern als viskositätsmodifikatoren Download PDFInfo
- Publication number
- EP4163305B1 EP4163305B1 EP22190123.4A EP22190123A EP4163305B1 EP 4163305 B1 EP4163305 B1 EP 4163305B1 EP 22190123 A EP22190123 A EP 22190123A EP 4163305 B1 EP4163305 B1 EP 4163305B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glucan
- poly alpha
- viscosity
- hydrocolloid
- aqueous solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000962 organic group Chemical group 0.000 claims description 53
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
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- 150000003522 tetracyclines Chemical class 0.000 description 1
- DCQJDRNKCUQEMA-UHFFFAOYSA-N tetradecanediperoxoic acid Chemical compound OOC(=O)CCCCCCCCCCCCC(=O)OO DCQJDRNKCUQEMA-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- LKHDXIBHVSGUHN-UHFFFAOYSA-N thiadiazole 1,1-dioxide Chemical class O=S1(=O)C=CN=N1 LKHDXIBHVSGUHN-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- VSJRDSLPNMGNFG-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate;trihydrate Chemical compound O.O.O.[Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O VSJRDSLPNMGNFG-UHFFFAOYSA-H 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000009492 vitamin B5 Nutrition 0.000 description 1
- 239000011675 vitamin B5 Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000001717 vitis vinifera seed extract Substances 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000037331 wrinkle reduction Effects 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 108010083879 xyloglucan endo(1-4)-beta-D-glucanase Proteins 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940006486 zinc cation Drugs 0.000 description 1
- 229940085658 zinc citrate trihydrate Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/225—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin etherified, e.g. CMC
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Definitions
- the invention concerns a method for increasing the viscosity of an aqueous composition.
- This method comprises contacting a poly alpha-1,3-glucan ether compound as disclosed herein with an aqueous composition, thereby increasing the viscosity of the aqueous composition.
- Poly alpha-1,3-glucan used to produce poly alpha-1,3-glucan ether compounds herein is preferably linear/unbranched.
- poly alpha-1,3-glucan has no branch points or less than about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1% branch points as a percent of the glycosidic linkages in the polymer.
- branch points include alpha-1,6 branch points, such as those present in mutan polymer.
- a poly alpha-1,3-glucan ether compound is termed an "ether" herein by virtue of comprising the substructure -C G -O-C-, where "-C G -" represents carbon 2, 4, or 6 of a glucose monomeric unit of a poly alpha-1,3-glucan ether compound, and where "-C-" is comprised in the organic group.
- Poly alpha-1,3-glucan ether compounds disclosed herein are synthetic, man-made compounds.
- an "organic group” group as used herein refers to a chain of one or more carbons that (i) has the formula -C n H 2n+1 (i.e., an alkyl group, which is completely saturated) or (ii) is mostly saturated but has one or more hydrogens substituted with another atom or functional group (i.e., a "substituted alkyl group”). Such substitution may be with one or more hydroxyl groups, oxygen atoms (thereby forming an aldehyde or ketone group), carboxyl groups, or other alkyl groups.
- a "halide” herein refers to a compound comprising one or more halogen atoms (e.g., fluorine, chlorine, bromine, iodine).
- a halide herein can refer to a compound comprising one or more halide groups such as fluoride, chloride, bromide, or iodide.
- a halide group may serve as a reactive group of an etherification agent.
- reaction refers to a reaction comprising at least poly alpha-1,3-glucan and an etherification agent. These components are typically dissolved and/or mixed in an aqueous alkali hydroxide. A reaction is placed under suitable conditions (e.g., time, temperature) for the etherification agent to etherify one or more hydroxyl groups of the glucose units of poly alpha-1,3-glucan with an organic group, thereby yielding a poly alpha-1,3-glucan ether compound.
- suitable conditions e.g., time, temperature
- poly alpha-1,3-glucan slurry refers to an aqueous mixture comprising the components of a glucosyltransferase enzymatic reaction such as poly alpha-1,3-glucan, sucrose, one or more glucosyltransferase enzymes, glucose and fructose.
- a glucosyltransferase enzymatic reaction such as poly alpha-1,3-glucan, sucrose, one or more glucosyltransferase enzymes, glucose and fructose.
- This composition is a slurry since the poly alpha-1,3-glucan is not dissolved therein.
- poly alpha-1,3-glucan wet cake herein refers to poly alpha-1,3-glucan that has been separated from a slurry and washed with water or an aqueous solution. Poly alpha-1,3-glucan is not completely dried when preparing a wet cake.
- degree of substitution refers to the average number of hydroxyl groups substituted in each monomeric unit (glucose) of a poly alpha-1,3-glucan ether compound. Since there are three hydroxyl groups in each monomeric unit in poly alpha-1,3-glucan, the degree of substitution in a poly alpha-1,3-glucan ether compound herein can be no higher than 3.
- crosslink refers to a chemical bond, atom, or group of atoms that connects two adjacent atoms in one or more polymer molecules. It should be understood that, in a composition comprising crosslinked poly alpha-1,3-glucan ether, crosslinks can be between at least two poly alpha-1,3-glucan ether molecules (i.e., intermolecular crosslinks); there can also be intramolecular crosslinking.
- a "crosslinking agent” as used herein is an atom or compound that can create crosslinks.
- aqueous composition refers to a solution or mixture in which the solvent is at least about 20 wt% water, for example, and which comprises poly alpha-1,3-glucan and/or a poly alpha-1,3-glucan ether compound.
- aqueous compositions herein are aqueous solutions and hydrocolloids.
- a 'dispersion refers to an aqueous composition comprising one or more particles (e.g., any ingredient of a personal care product, pharmaceutical product, food product, household product, or industrial product disclosed herein) that are scattered, or uniformly scattered, throughout the aqueous composition. It is believed that poly alpha-1,3-glucan and/or poly alpha-1,3-glucan ether compounds can act as dispersants in aqueous compositions disclosed herein.
- contacting refers to any action that results in bringing together an aqueous composition with poly alpha-1,3-glucan and/or a poly alpha-1,3-glucan ether compound. Contacting can be performed by any means known in the art, such as dissolving, mixing, shaking, or homogenization, for example.
- fabric refers to a woven material having a network of natural and/or artificial fibers.
- Such fibers can be thread or yarn, for example.
- a “fabric care composition” herein is any composition suitable for treating fabric in some manner.
- Examples of such a composition include laundry detergents and fabric softeners.
- heavy duty detergent and “all-purpose detergent” are used interchangeably herein to refer to a detergent useful for regular washing of white and colored textiles at any temperature.
- low duty detergent or “fine fabric detergent” are used interchangeably herein to refer to a detergent useful for the care of delicate fabrics such as viscose, wool, silk, microfiber or other fabric requiring special care.
- Special care can include conditions of using excess water, low agitation, and/or no bleach, for example.
- oral care composition herein is any composition suitable for treating an soft or hard surface in the oral cavity such as dental (teeth) and/or gum surfaces.
- adsorption herein refers to the adhesion of a compound (e.g., poly alpha-1,3-glucan ether) to the surface of a material.
- the "molecular weight" of poly alpha-1,3-glucan and poly alpha-1,3-glucan ether compounds herein can be represented as number-average molecular weight (M n ) or as weight-average molecular weight (M w ).
- M n number-average molecular weight
- M w weight-average molecular weight
- molecular weight can be represented as Daltons, grams/mole, DPw (weight average degree of polymerization), or DPn (number average degree of polymerization).
- DPw weight average degree of polymerization
- DPn number average degree of polymerization
- percent by volume percent by volume
- volume percent percent by volume
- vol % percent by volume
- v/v % percent by volume
- Embodiments of the disclosed invention concern a hydrocolloid or aqueous solution comprising a poly alpha-1,3-glucan ether compound represented by the structure:
- the DoS of a poly alpha-1,3-glucan ether compound disclosed herein can affect the viscosity of the hydrocolloid or aqueous solution comprising the compound.
- a hydrocolloid or aqueous solution comprising carboxymethyl poly alpha-1,3-glucan (CMG) with a DoS of about 0.4-0.6 has greater viscosity than a hydrocolloid or aqueous solution comprising CMG with higher DoS (e.g., about 0.8-1.0).
- n can have a value of at least 25, 50, 75, 100, 150, 200, 250, 300, 350, 400, 450, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, or 4000 (or any integer between 25 and 4000), for example.
- n in still other examples can be in a range of 25-250, 50-250, 75-250, 100-250, 150-250, 200-250, 25-200, 50-200, 75-200, 100-200, 150-200, 25-150, 50-150, 75-150, 100-150, 25-100, 50-100, 75-100, 25-75, 50-75, or 25-50.
- dihydroxy alkyl groups such as dihydroxymethyl, dihydroxyethyl (e.g., -CH(OH)CH 2 OH), dihydroxypropyl (e.g., -CH 2 CH(OH)CH 2 OH, -CH(OH)CH(OH)CH 3 ), dihydroxybutyl and dihydroxypentyl groups.
- one or more carbons of an alkyl group can have a substitution(s) with another alkyl group.
- substituent alkyl groups are methyl, ethyl and propyl groups.
- an R group can be -CH(CH 3 )CH 2 CH 3 or -CH 2 CH(CH 3 )CH 3 , for example, which are both propyl groups having a methyl substitution.
- a substitution (e.g., hydroxy or carboxy group) on an alkyl group in certain embodiments may be bonded to the terminal carbon atom of the alkyl group, where the terminal carbon group is opposite the terminus that is in ether linkage to the glucose group in the glucan ether compound (above formula).
- An example of this terminal substitution is in the hydroxypropyl group -CH 2 CH 2 CH 2 OH.
- a substitution may be on an internal carbon atom of an alkyl group.
- An example on an internal substitution is in the hydroxypropyl group -CH 2 CH(OH)CH 3 .
- An alkyl group can have one or more substitutions, which may be the same (e.g., two hydroxyl groups [dihydroxy]) or different (e.g., a hydroxyl group and a carboxyl group).
- Hydrocolloids or aqueous solutions comprising a poly alpha-1,3-glucan ether compound disclosed herein have a viscosity of at least about 10 cPs.
- a hydrocolloid or aqueous solution herein has a viscosity of at least about 100, 250, 500, 750, 1000, 1500, 2000, 2500, 3000, 3500, 4000, 4500, 5000, 5500, 6000, 6500, 7000, 7500, 8000, 8500, 9000, 9500, 10000, 10500, 11000, 12000, 13000, 14000, 15000, 20000, 30000, 40000, 50000, 60000, 70000, 80000, 90000, or 100000 cPs (or any integer between 100 and 100000 cPs), for example.
- Viscosity can be measured with the hydrocolloid or aqueous solution at any temperature between about 3 °C to about 110 °C (or any integer between 3 and 110 °C), for example. Alternatively, viscosity can be measured at a temperature between about 4 °C to 30 °C, or about 20 °C to 25 °C. Viscosity can be measured at atmospheric pressure (about 760 torr) or any other higher or lower pressure.
- the viscosity of a hydrocolloid or aqueous solution disclosed herein can be measured using a viscometer or rheometer, or using any other means known in the art. It would be understood by those skilled in the art that a rheometer can be used to measure the viscosity of those hydrocolloids and aqueous solutions of the invention that exhibit shear thinning behavior or shear thickening behavior (i.e., liquids with viscosities that vary with flow conditions).
- the viscosity of such embodiments can be measured at a rotational shear rate of about 10 to 1000 rpm (revolutions per minute) (or any integer between 10 and 1000 rpm), for example.
- viscosity can be measured at a rotational shear rate of about 10, 60, 150, 250, or 600 rpm.
- a poly alpha-1,3-glucan ether compound can be in an anionic form in a hydrocolloid or aqueous solution.
- examples may include those poly alpha-1,3-glucan ether compounds having an organic group comprising an alkyl group substituted with a carboxyl group.
- Carboxyl (COOH) groups in a carboxyalkyl poly alpha-1,3-glucan ether compound can convert to carboxylate (COO - ) groups in aqueous conditions.
- Such anionic groups can interact with salt cations such as any of those listed above in (i) (e.g., potassium, sodium, or lithium cation).
- a poly alpha-1,3-glucan ether compound can be a sodium carboxyalkyl poly alpha-1,3-glucan ether (e.g., sodium carboxymethyl poly alpha-1,3-glucan), potassium carboxyalkyl poly alpha-1,3-glucan ether (e.g., potassium carboxymethyl poly alpha-1,3-glucan), or lithium carboxyalkyl poly alpha-1,3-glucan ether (e.g., lithium carboxymethyl poly alpha-1,3-glucan), for example.
- sodium carboxyalkyl poly alpha-1,3-glucan ether e.g., sodium carboxymethyl poly alpha-1,3-glucan
- potassium carboxyalkyl poly alpha-1,3-glucan ether e.g., potassium carboxymethyl poly alpha-1,3-glucan
- lithium carboxyalkyl poly alpha-1,3-glucan ether e.g., lithium carboxymethyl poly alpha-1,3-glucan
- a composition comprising poly alpha-1,3-glucan and/or a poly alpha-1,3-glucan ether compound herein can be non-aqueous (e.g., a dry composition).
- non-aqueous or dry composition typically has less than 3, 2, 1, 0.5, or 0.1 wt% water comprised therein.
- a poly alpha-1,3-glucan ether compound comprised in certain embodiments of the disclosed composition may be crosslinked using any means known in the art.
- Such crosslinks may be borate crosslinks, where the borate is from any boron-containing compound (e.g., boric acid, diborates, tetraborates, pentaborates, polymeric compounds such as Polybor ® , polymeric compounds of boric acid, alkali borates), for example.
- crosslinks can be provided with polyvalent metals such as titanium or zirconium. Titanium crosslinks may be provided, for example, using titanium IV-containing compounds such as titanium ammonium lactate, titanium triethanolamine, titanium acetylacetonate, and polyhydroxy complexes of titanium.
- Zirconium crosslinks can be provided using zirconium IV-containing compounds such as zirconium lactate, zirconium carbonate, zirconium acetylacetonate, zirconium triethanolamine, zirconium diisopropylamine lactate and polyhydroxy complexes of zirconium, for example.
- crosslinks can be provided with any crosslinking agent described in U.S. Patent Nos. 4462917 , 4464270 , 4477360 and 4799550 .
- a crosslinking agent e.g., borate
- a crosslinking agent may be present in an aqueous composition herein at a concentration of about 0.2% to 20 wt%, or about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, or 20 wt%, for example.
- a composition herein may optionally contain one or more active enzymes.
- suitable enzymes include proteases, cellulases, hemicellulases, peroxidases, lipolytic enzymes (e.g., metallolipolytic enzymes), xylanases, lipases, phospholipases, esterases (e.g., arylesterase, polyesterase), perhydrolases, cutinases, pectinases, pectate lyases, mannanases, keratinases, reductases, oxidases (e.g., choline oxidase), phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, arabinosidases, hyaluronidases, chondroitinases, laccases, metalloproteinases, amadoria
- a cellulase herein may be derived from any microbial source, such as a bacteria or fungus. Chemically-modified cellulases or protein-engineered mutant cellulases are included. Suitable cellulases include, but are not limited to, cellulases from the genera Bacillus , Pseudomonas , Streptomyces , Trichoderma , Humicola , Fusarium , Thielavia and Acremonium. As other examples, a cellulase may be derived from Humicola insolens , Myceliophthora thermophila or Fusarium oxysporum ; these and other cellulases are disclosed in U.S. Patent Nos.
- Exemplary Trichoderma reesei cellulases are disclosed in U.S. Patent Nos. 4689297 , 5814501 , 5324649 , and International Patent Appl. Publ. Nos. WO92/06221 and WO92/06165 .
- Exemplary Bacillus cellulases are disclosed in U.S. Patent No. 6562612 .
- a cellulase, such as any of the foregoing, preferably is in a mature form lacking an N-terminal signal peptide.
- One or more cellulases can be directly added as an ingredient when preparing the disclosed composition.
- one or more cellulases can be indirectly (inadvertently) provided in the disclosed composition.
- cellulase can be provided in a composition herein by virtue of being present in a non-cellulase enzyme preparation used for preparing the composition.
- Cellulase in compositions in which cellulase is indirectly provided thereto can be present at about 0.1-10 ppb (e.g., less than 1 ppm), for example.
- a benefit of a composition herein by virtue of employing a poly alpha-1,3-glucan ether compound instead of a cellulose ether compound, is that non-cellulase enzyme preparations that might have background cellulase activity can be used without concern that the desired effects of the glucan ether will be negated by the background cellulase activity.
- a cellulase in certain embodiments can be thermostable.
- Cellulase thermostability refers to the ability of the enzyme to retain activity after exposure to an elevated temperature (e.g. about 60-70 °C) for a period of time (e.g., about 30-60 minutes).
- the thermostability of a cellulase can be measured by its half-life (t1/2) given in minutes, hours, or days, during which time period half the cellulase activity is lost under defined conditions.
- a cellulase in certain embodiments can be stable to a wide range of pH values (e.g. neutral or alkaline pH such as pH of ⁇ 7.0 to ⁇ 11.0). Such enzymes can remain stable for a predetermined period of time (e.g., at least about 15 min., 30 min., or 1 hour) under such pH conditions.
- pH values e.g. neutral or alkaline pH such as pH of ⁇ 7.0 to ⁇ 11.0.
- Such enzymes can remain stable for a predetermined period of time (e.g., at least about 15 min., 30 min., or 1 hour) under such pH conditions.
- At least one, two, or more cellulases may be included in the composition, for example.
- the total amount of cellulase in a composition herein typically is an amount that is suitable for the purpose of using cellulase in the composition (an "effective amount").
- an effective amount of cellulase in a composition intended for improving the feel and/or appearance of a cellulose-containing fabric is an amount that produces measurable improvements in the feel of the fabric (e.g., improving fabric smoothness and/or appearance, removing pills and fibrils which tend to reduce fabric appearance sharpness).
- an effective amount of cellulase in a fabric stonewashing composition herein is that amount which will provide the desired effect (e.g., to produce a worn and faded look in seams and on fabric panels).
- the amount of cellulase in a composition herein can also depend on the process parameters in which the composition is employed (e.g., equipment, temperature, time, and the like) and cellulase activity, for example.
- the effective concentration of cellulase in an aqueous composition in which a fabric is treated can be readily determined by a skilled artisan.
- Personal care products herein are not particularly limited and include, for example, skin care compositions, cosmetic compositions, antifungal compositions, and antibacterial compositions.
- Personal care products herein may be in the form of, for example, lotions, creams, pastes, balms, ointments, pomades, gels, liquids, combinations of these and the like.
- the personal care products disclosed herein can include at least one active ingredient, if desired.
- An active ingredient is generally recognized as an ingredient that causes an intended pharmacological effect.
- a detergent composition herein may be in any useful form, e.g., as powders, granules, pastes, bars, unit dose, or liquid.
- a liquid detergent may be aqueous, typically containing up to about 70 wt% of water and 0 wt% to about 30 wt% of organic solvent. It may also be in the form of a compact gel type containing only about 30 wt% water.
- Builders include, but are not limited to, alkali metal, ammonium and alkanolammonium salts of polyphosphates, alkali metal silicates, alkaline earth and alkali metal carbonates, aluminosilicates, polycarboxylate compounds, ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1, 3, 5-trihydroxy benzene-2, 4, 6-trisulphonic acid, and carboxymethyloxysuccinic acid, various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid, as well as polycarboxylates such as mellitic acid, succinic acid, citric acid, oxydisuccinic acid, polymaleic acid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof.
- a detergent composition herein can comprise at least one chelating agent.
- Suitable chelating agents include, but are not limited to copper, iron and/or manganese chelating agents and mixtures thereof.
- the composition comprises from about 0.1% to about 15%, or even from about 3.0% to about 10%, chelating agent by weight of the composition.
- Suitable proteases include those of animal, vegetable or microbial origin. In some embodiments, microbial proteases are used. In some embodiments, chemically or genetically modified mutants are included.
- the protease is a serine protease, preferably an alkaline microbial protease or a trypsin-like protease.
- alkaline proteases include subtilisins, especially those derived from Bacillus (e.g., subtilisin, lentus, amyloliquefaciens, subtilisin Carlsberg, subtilisin 309, subtilisin 147 and subtilisin 168). Additional examples include those mutant proteases described in U.S. Pat. Nos.
- cloned lipases find use in some embodiments of the present invention, including but not limited to, Penicillium camembertii lipase (See, Yamaguchi et al., Gene 103:61-67 [1991 ]), Geotricum candidum lipase (See, Schimada et al., J. Biochem., 106:383-388 [1989 ]), and various Rhizopus lipases such as R. delemar lipase (See, Hass et al., Gene 109:117-113 [1991 ]), a R. niveus lipase ( Kugimiya et al., Biosci. Biotech. Biochem.
- Additional lipases useful herein include, for example, those disclosed in WO92/05249 , WO94/01541 , WO95/35381 , WO96/00292 , WO95/30744 , WO94/25578 , WO95/14783 , WO95/22615 , WO97/04079 , WO97/07202 , EP407225 and EP260105 .
- Suitable polyesterases include, for example, those disclosed in WO01/34899 , WO01/14629 and U.S. Patent No. 6933140 .
- a detergent composition herein can also comprise 2,6-beta-D-fructan hydrolase, which is effective for removal/cleaning of certain biofilms present on household and/or industrial textiles/laundry.
- Additional suitable amylases include those disclosed in WO9510603 , WO9526397 , WO9623874 , WO9623873 , WO9741213 , WO9919467 , WO0060060 , WO0029560 , WO9923211 , WO9946399 , WO0060058 , WO0060059 , WO9942567 , WO0114532 , WO02092797 , WO0166712 , WO0188107 , WO0196537 , WO0210355 , WO9402597 , WO0231124 , WO9943793 , WO9943794 , WO2004113551 , WO2005001064 , WO2005003311 , WO0164852 , WO2006063594 , WO2006066594 , WO2006066596 , WO2006012899 , WO20080929
- Suitable amylases include, for example, commercially available amylases such as STAINZYME ® , STAINZYME PLUS ® , NATALASE ® , DURAMYL ® , TERMAMYL ® , TERMAMYL ULTRA ® , FUNGAMYL ® and BAN TM (Novo Nordisk A/S and Novozymes A/S); RAPIDASE ® , POWERASE ® , PURASTAR ® and PREFERENZ TM (DuPont Industrial Biosciences).
- Suitable peroxidases/oxidases contemplated for use in the compositions include those of plant, bacterial or fungal origin. Chemically modified or protein engineered mutants are included. Examples of peroxidases useful herein include those from the genus Coprinus (e.g., C. cinereus , WO93/24618 , WO95/10602 , and WO98/15257 ), as well as those referenced in WO2005056782 , WO2007106293 , WO2008063400 , WO2008106214 , and WO2008106215 . Commercially available peroxidases useful herein include, for example, GUARDZYME TM (Novo Nordisk A/S and Novozymes A/S).
- peroxidases are used in combination with hydrogen peroxide or a source thereof (e.g., a percarbonate, perborate or persulfate) in the compositions of the present invention.
- oxidases are used in combination with oxygen. Both types of enzymes are used for "solution bleaching" (i.e., to prevent transfer of a textile dye from a dyed fabric to another fabric when the fabrics are washed together in a wash liquor), preferably together with an enhancing agent (See e.g., WO94/12621 and WO95/01426 ).
- Suitable peroxidases/oxidases include, but are not limited to, those of plant, bacterial or fungal origin. Chemically or genetically modified mutants are included in some embodiments.
- Enzymes that may be comprised in a detergent composition herein may be stabilized using conventional stabilizing agents, e.g., a polyol such as propylene glycol or glycerol; a sugar or sugar alcohol; lactic acid; boric acid or a boric acid derivative (e.g., an aromatic borate ester).
- a polyol such as propylene glycol or glycerol
- a sugar or sugar alcohol lactic acid
- boric acid or a boric acid derivative e.g., an aromatic borate ester
- a detergent composition herein may contain about 1 wt% to about 65 wt% of a detergent builder or complexing agent such as zeolite, diphosphate, triphosphate, phosphonate, citrate, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTMPA), alkyl- or alkenylsuccinic acid, soluble silicates or layered silicates (e.g., SKS-6 from Hoechst).
- a detergent may also be unbuilt, i.e., essentially free of detergent builder.
- a detergent composition in certain embodiments may comprise one or more other types of polymers in addition to a poly alpha-1,3-glucan and/or poly alpha-1,3-glucan ether compound.
- examples of other types of polymers useful herein include carboxymethyl cellulose (CMC), poly(vinylpyrrolidone) (PVP), polyethylene glycol (PEG), poly(vinyl alcohol) (PVA), polycarboxylates such as polyacrylates, maleic/acrylic acid copolymers and lauryl methacrylate/acrylic acid copolymers.
- a detergent composition herein may contain a bleaching system.
- a bleaching system can comprise an H 2 O 2 source such as perborate or percarbonate, which may be combined with a peracid-forming bleach activator such as tetraacetylethylenediamine (TAED) or nonanoyloxybenzenesulfonate (NOBS).
- TAED tetraacetylethylenediamine
- NOBS nonanoyloxybenzenesulfonate
- TAED tetraacetylethylenediamine
- NOBS nonanoyloxybenzenesulfonate
- a bleaching system may comprise peroxyacids (e.g., amide, imide, or sulfone type peroxyacids).
- a bleaching system can be an enzymatic bleaching system comprising perhydrolase, for example, such as the system described in WO2005/056783 .
- a detergent composition herein may also contain conventional detergent ingredients such as fabric conditioners, clays, foam boosters, suds suppressors, anti-corrosion agents, soil-suspending agents, anti-soil redeposition agents, dyes, bactericides, tarnish inhibitors, optical brighteners, or perfumes.
- the pH of a detergent composition herein is usually neutral or alkaline (e.g., pH of about 7.0 to about 11.0).
- detergent compositions that can be adapted for purposes disclosed herein are disclosed in, for example, US20090209445A1 , US20100081598A1 , US7001878B2 , EP1504994B1 , WO2001085888A2 , WO2003089562A1 , WO2009098659A1 , WO2009098660A1 , WO2009112992A1 , WO2009124160A1 , WO2009152031A1 , WO2010059483A1 , WO2010088112A1 , WO2010090915A1 , WO2010135238A1 , WO2011094687A1 , WO2011094690A1 , WO2011127102A1 , WO2011163428A1 , WO2008000567A1 , WO2006045391A1 , WO2006007911A1 , WO2012027404A1 , EP1740690B1 , WO
- Laundry detergent compositions herein can optionally be heavy duty (all purpose) laundry detergent compositions.
- exemplary heavy duty laundry detergent compositions comprise a detersive surfactant (10%-40% wt/wt), including an anionic detersive surfactant (selected from a group of linear or branched or random chain, substituted or unsubstituted alkyl sulphates, alkyl sulphonates, alkyl alkoxylated sulphate, alkyl phosphates, alkyl phosphonates, alkyl carboxylates, and/or mixtures thereof), and optionally non-ionic surfactant (selected from a group of linear or branched or random chain, substituted or unsubstituted alkyl alkoxylated alcohol, e.g., C8-C18 alkyl ethoxylated alcohols and/or C6-C12 alkyl phenol alkoxylates), where the weight ratio of anionic detersive surfactant (with a
- Suitable detersive surfactants also include cationic detersive surfactants (selected from a group of alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, alkyl ternary sulphonium compounds, and/or mixtures thereof); zwitterionic and/or amphoteric detersive surfactants (selected from a group of alkanolamine sulpho-betaines); ampholytic surfactants; semi-polar non-ionic surfactants and mixtures thereof.
- cationic detersive surfactants selected from a group of alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, alkyl ternary sulphonium compounds, and/or mixtures thereof
- zwitterionic and/or amphoteric detersive surfactants selected from a group of alkanolamine sulpho-betaines
- a detergent herein such as a heavy duty laundry detergent composition may optionally include additional polymers such as soil release polymers (include anionically end-capped polyesters, for example SRP1, polymers comprising at least one monomer unit selected from saccharide, dicarboxylic acid, polyol and combinations thereof, in random or block configuration, ethylene terephthalate-based polymers and co-polymers thereof in random or block configuration, for example REPEL-O-TEX SF, SF-2 AND SRP6, TEXCARE SRA100, SRA300, SRN100, SRN170, SRN240, SRN300 AND SRN325, MARLOQUEST SL), antiredeposition polymers (0.1 wt% to 10 wt%), include carboxylate polymers, such as polymers comprising at least one monomer selected from acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, methylenemalonic acid,
- a detergent herein such as a heavy duty laundry detergent composition may optionally further include dye transfer inhibiting agents, examples of which include manganese phthalocyanine, peroxidases, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles and/or mixtures thereof; chelating agents, examples of which include ethylene-diamine-tetraacetic acid (EDTA), diethylene triamine penta methylene phosphonic acid (DTPMP), hydroxy-ethane diphosphonic acid (HEDP), ethylenediamine N,N'-disuccinic acid (EDDS), methyl glycine diacetic acid (MGDA), diethylene triamine penta acetic acid (DTPA), propylene diamine tetracetic acid (PDTA), 2-hydroxypyridine-N-oxide (HPNO), or methyl g
- a detergent herein such as a heavy duty laundry detergent composition may optionally include silicone or fatty-acid based suds suppressors; hueing dyes, calcium and magnesium cations, visual signaling ingredients, anti-foam (0.001 wt% to about 4.0 wt%), and/or a structurant/thickener (0.01 wt% to 5 wt%) selected from the group consisting of diglycerides and triglycerides, ethylene glycol distearate, microcrystalline cellulose, microfiber cellulose, biopolymers, xanthan gum, gellan gum, and mixtures thereof).
- Such structurant/thickener would be in addition to the one or more poly alpha-1,3-glucan compounds comprised in the detergent.
- a detergent herein can be in the form of a heavy duty dry/solid laundry detergent composition, for example.
- a detergent may include: (i) a detersive surfactant, such as any anionic detersive surfactant disclosed herein, any non-ionic detersive surfactant disclosed herein, any cationic detersive surfactant disclosed herein, any zwitterionic and/or amphoteric detersive surfactant disclosed herein, any ampholytic surfactant, any semi-polar non-ionic surfactant, and mixtures thereof; (ii) a builder, such as any phosphate-free builder (e.g., zeolite builders in the range of 0 wt% to less than 10 wt%), any phosphate builder (e.g., sodium tri-polyphosphate in the range of 0 wt% to less than 10 wt%), citric acid, citrate salts and nitrilotriacetic acid, any silicate salt (e.g., sodium
- compositions disclosed herein can be in the form of a dishwashing detergent composition.
- dishwashing detergents include automatic dishwashing detergents (typically used in dishwasher machines) and hand-washing dish detergents.
- a dishwashing detergent composition can be in any dry or liquid/aqueous form as disclosed herein, for example.
- Components that may be included in certain embodiments of a dishwashing detergent composition include, for example, one or more of a phosphate; oxygen- or chlorine-based bleaching agent; non-ionic surfactant; alkaline salt (e.g., metasilicates, alkali metal hydroxides, sodium carbonate); any active enzyme disclosed herein; anti-corrosion agent (e.g., sodium silicate); anti-foaming agent; additives to slow down the removal of glaze and patterns from ceramics; perfume; anti-caking agent (in granular detergent); starch (in tablet-based detergents); gelling agent (in liquid/gel based detergents); and/or sand (powdered detergents).
- alkaline salt e.g., metasilicates, alkali metal hydroxides, sodium carbonate
- anti-corrosion agent e.g., sodium silicate
- anti-foaming agent additives to slow down the removal of glaze and patterns from ceramics
- perfume anti-caking agent (in
- Dishwashing detergents such as an automatic dishwasher detergent or liquid dishwashing detergent can comprise (i) a non-ionic surfactant, including any ethoxylated non-ionic surfactant, alcohol alkoxylated surfactant, epoxy-capped poly(oxyalkylated) alcohol, or amine oxide surfactant present in an amount from 0 to 10 wt%; (ii) a builder, in the range of about 5-60 wt%, including any phosphate builder (e.g., mono-phosphates, di-phosphates, tri-polyphosphates, other oligomeric-polyphosphates, sodium tripolyphosphate-STPP), any phosphate-free builder (e.g., amino acid-based compounds including methyl-glycine-diacetic acid [MGDA] and salts or derivatives thereof, glutamic-N,N-diacetic acid [GLDA] and salts or derivatives thereof, iminodisuccinic acid (IDS) and salts
- detergent formulations comprising at least one poly alpha-1,3-glucan ether compound (e.g., a carboxyalkyl poly alpha-1,3-glucan ether such as carboxymethyl poly alpha-1,3-glucan [CMG]) are disclosed below (1-19):
- a poly alpha-1,3-glucan ether compound e.g., a carboxyalkyl poly alpha-1,3-glucan ether such as carboxymethyl poly alpha-1,3-glucan [CMG]
- detergent formulations can be adapted to include a poly alpha-1,3-glucan ether compound.
- examples include PUREX ® ULTRAPACKS (Henkel), FINISH ® QUANTUM (Reckitt Benckiser), CLOROX TM 2 PACKS (Clorox), OXICLEAN MAX FORCE POWER PAKS (Church & Dwight), TIDE ® STAIN RELEASE, CASCADE ® ACTIONPACS, and TIDE ® PODS TM (Procter & Gamble).
- compositions disclosed herein can be in the form of an oral care composition.
- oral care compositions include dentifrices, toothpaste, mouth wash, mouth rinse, chewing gum, and edible strips that provide some form of oral care (e.g., treatment or prevention of cavities [dental caries], gingivitis, plaque, tartar, and/or periodontal disease).
- An oral care composition can also be for treating an "oral surface", which encompasses any soft or hard surface within the oral cavity including surfaces of the tongue, hard and soft palate, buccal mucosa, gums and dental surfaces.
- a "dental surface” herein is a surface of a natural tooth or a hard surface of artificial dentition including a crown, cap, filling, bridge, denture, or dental implant, for example.
- One or more poly alpha-1,3-glucan and/or poly alpha-1,3-glucan ether compounds comprised in an oral care composition typically are provided therein as a thickening agent and/or dispersion agent, which may be useful to impart a desired consistency and/or mouth feel to the composition.
- An oral care composition herein can comprise about 0.01-15.0 wt% (e.g., -0.1-10 wt% or -0.1-5.0 wt%, -0.1-2.0 wt%) of one or more poly alpha-1,3-glucan and/or poly alpha-1,3-glucan ether compounds disclosed herein (e.g., a carboxyalkyl poly alpha-1,3-glucan ether such as carboxymethyl poly alpha-1,3-glucan [CMG]), for example.
- poly alpha-1,3-glucan and/or poly alpha-1,3-glucan ether compounds disclosed herein e.g., a carboxyalkyl poly alpha-1,3-glucan ether such as carboxymethyl poly alpha-1,3-glucan [CMG]
- One or more other thickening agents or dispersion agents can also be provided in an oral care composition herein, such as a carboxyvinyl polymer, carrageenan (e.g., L-carrageenan), natural gum (e.g., karaya, xanthan, gum arabic, tragacanth), colloidal magnesium aluminum silicate, or colloidal silica, for example.
- carrageenan e.g., L-carrageenan
- natural gum e.g., karaya, xanthan, gum arabic, tragacanth
- colloidal magnesium aluminum silicate e.g., colloidal magnesium aluminum silicate, or colloidal silica, for example.
- An oral care composition herein may be a toothpaste or other dentifrice, for example.
- Such compositions, as well as any other oral care composition herein can additionally comprise, without limitation, one or more of an anticaries agent, antimicrobial or antibacterial agent, anticalculus or tartar control agent, surfactant, abrasive, pH-modifying agent, foam modulator, humectant, flavorant, sweetener, pigment/colorant, whitening agent, and/or other suitable components.
- Examples of oral care compositions to which one or more poly alpha-1,3-glucan ether compounds can be added are disclosed in U.S. Patent Appl. Publ. Nos. 2006/0134025 , 2002/0022006 and 2008/0057007 .
- An anticaries agent herein can be an orally acceptable source of fluoride ions.
- Suitable sources of fluoride ions include fluoride, monofluorophosphate and fluorosilicate salts as well as amine fluorides, including olaflur (N'-octadecyltrimethylendiamine-N,N,N'- tris(2-ethanol)-dihydrofluoride), for example.
- An anticaries agent can be present in an amount providing a total of about 100-20000 ppm, about 200-5000 ppm, or about 500-2500 ppm, fluoride ions to the composition, for example.
- sodium fluoride is the sole source of fluoride ions
- an amount of about 0.01-5.0 wt%, about 0.05-1.0 wt%, or about 0.1-0.5 wt%, sodium fluoride can be present in the composition, for example.
- An antimicrobial or antibacterial agent suitable for use in an oral care composition herein includes, for example, phenolic compounds (e.g., 4-allylcatechol; p-hydroxybenzoic acid esters such as benzylparaben, butylparaben, ethylparaben, methylparaben and propylparaben; 2-benzylphenol; butylated hydroxyanisole; butylated hydroxytoluene; capsaicin; carvacrol; creosol; eugenol; guaiacol; halogenated bisphenolics such as hexachlorophene and bromochlorophene; 4-hexylresorcinol; 8-hydroxyquinoline and salts thereof; salicylic acid esters such as menthyl salicylate, methyl salicylate and phenyl salicylate; phenol; pyrocatechol; salicylanilide; thymol; halogenated diphenylether compounds such as tric
- One or more antimicrobial agents can optionally be present at about 0.01-10 wt% (e
- Useful inorganic phosphate and polyphosphate salts include, for example, monobasic, dibasic and tribasic sodium phosphates, sodium tripolyphosphate, tetrapolyphosphate, mono-, di-, tri- and tetra-sodium pyrophosphates, disodium dihydrogen pyrophosphate, sodium trimetaphosphate, sodium hexametaphosphate, or any of these in which sodium is replaced by potassium or ammonium.
- Other useful anticalculus agents in certain embodiments include anionic polycarboxylate polymers (e.g., polymers or copolymers of acrylic acid, methacrylic, and maleic anhydride such as polyvinyl methyl ether/maleic anhydride copolymers).
- Still other useful anticalculus agents include sequestering agents such as hydroxycarboxylic acids (e.g., citric, fumaric, malic, glutaric and oxalic acids and salts thereof) and aminopolycarboxylic acids (e.g., EDTA).
- hydroxycarboxylic acids e.g., citric, fumaric, malic, glutaric and oxalic acids and salts thereof
- aminopolycarboxylic acids e.g., EDTA
- One or more anticalculus or tartar control agents can optionally be present at about 0.01-50 wt% (e.g., about 0.05-25 wt% or about 0.1-15 wt%), for example, in the disclosed oral care composition.
- a surfactant suitable for use in an oral care composition herein may be anionic, non-ionic, or amphoteric, for example.
- Suitable anionic surfactants include, without limitation, water-soluble salts of C 8-20 alkyl sulfates, sulfonated monoglycerides of C 8-20 fatty acids, sarcosinates, and taurates.
- anionic surfactants include sodium lauryl sulfate, sodium coconut monoglyceride sulfonate, sodium lauryl sarcosinate, sodium lauryl isoethionate, sodium laureth carboxylate and sodium dodecyl benzenesulfonate.
- Suitable non-ionic surfactants include, without limitation, poloxamers, polyoxyethylene sorbitan esters, fatty alcohol ethoxylates, alkylphenol ethoxylates, tertiary amine oxides, tertiary phosphine oxides, and dialkyl sulfoxides.
- Suitable amphoteric surfactants include, without limitation, derivatives of C 8-20 aliphatic secondary and tertiary amines having an anionic group such as a carboxylate, sulfate, sulfonate, phosphate or phosphonate.
- An example of a suitable amphoteric surfactant is cocoamidopropyl betaine.
- One or more surfactants are optionally present in a total amount of about 0.01-10 wt% (e.g., about 0.05-5.0 wt% or about 0.1-2.0 wt%), for example, in the disclosed oral care composition.
- An abrasive suitable for use in an oral care composition herein may include, for example, silica (e.g., silica gel, hydrated silica, precipitated silica), alumina, insoluble phosphates, calcium carbonate, and resinous abrasives (e.g., a urea-formaldehyde condensation product).
- silica e.g., silica gel, hydrated silica, precipitated silica
- alumina e.g., insoluble phosphates, calcium carbonate
- resinous abrasives e.g., a urea-formaldehyde condensation product
- insoluble phosphates useful as abrasives herein are orthophosphates, polymetaphosphates and pyrophosphates, and include dicalcium orthophosphate dihydrate, calcium pyrophosphate, beta-calcium pyrophosphate, tricalcium phosphate, calcium polymetaphosphate and insoluble sodium polymeta
- One or more abrasives are optionally present in a total amount of about 5-70 wt% (e.g., about 10-56 wt% or about 15-30 wt%), for example, in the disclosed oral care composition.
- the average particle size of an abrasive in certain embodiments is about 0.1-30 microns (e.g., about 1-20 microns or about 5-15 microns).
- An oral care composition in certain embodiments may comprise at least one pH-modifying agent.
- pH-modifying agents may be selected to acidify, make more basic, or buffer the pH of a composition to a pH range of about 2-10 (e.g., pH ranging from about 2-8, 3-9, 4-8, 5-7, 6-10, or 7-9).
- pH-modifying agents useful herein include, without limitation, carboxylic, phosphoric and sulfonic acids; acid salts (e.g., monosodium citrate, disodium citrate, monosodium malate); alkali metal hydroxides (e.g.
- sodium hydroxide carbonates such as sodium carbonate, bicarbonates, sesquicarbonates); borates; silicates; phosphates (e.g., monosodium phosphate, trisodium phosphate, pyrophosphate salts); and imidazole.
- a foam modulator suitable for use in an oral care composition herein may be a polyethylene glycol (PEG), for example.
- PEG polyethylene glycol
- High molecular weight PEGs are suitable, including those having an average molecular weight of about 200000-7000000 (e.g., about 500000-5000000 or about 1000000-2500000), for example.
- One or more PEGs are optionally present in a total amount of about 0.1-10 wt% (e.g. about 0.2-5.0 wt% or about 0.25-2.0 wt%), for example, in the disclosed oral care composition.
- An oral care composition in certain embodiments may comprise at least one humectant.
- a humectant in certain embodiments may be a polyhydric alcohol such as glycerin, sorbitol, xylitol, or a low molecular weight PEG. Most suitable humectants also may function as a sweetener herein.
- One or more humectants are optionally present in a total amount of about 1.0-70 wt% (e.g., about 1.0-50 wt%, about 2-25 wt%, or about 5-15 wt%), for example, in the disclosed oral care composition.
- a natural or artificial sweetener may optionally be comprised in an oral care composition herein.
- suitable sweeteners include dextrose, sucrose, maltose, dextrin, invert sugar, mannose, xylose, ribose, fructose, levulose, galactose, corn syrup (e.g., high fructose corn syrup or corn syrup solids), partially hydrolyzed starch, hydrogenated starch hydrolysate, sorbitol, mannitol, xylitol, maltitol, isomalt, aspartame, neotame, saccharin and salts thereof, dipeptide-based intense sweeteners, and cyclamates.
- One or more sweeteners are optionally present in a total amount of about 0.005-5.0 wt%, for example, in the disclosed oral care composition.
- a natural or artificial flavorant may optionally be comprised in an oral care composition herein.
- suitable flavorants include vanillin; sage; marjoram; parsley oil; spearmint oil; cinnamon oil; oil of wintergreen (methylsalicylate); peppermint oil; clove oil; bay oil; anise oil; eucalyptus oil; citrus oils; fruit oils; essences such as those derived from lemon, orange, lime, grapefruit, apricot, banana, grape, apple, strawberry, cherry, or pineapple; bean- and nut-derived flavors such as coffee, cocoa, cola, peanut, or almond; and adsorbed and encapsulated flavorants.
- ingredients that provide fragrance and/or other sensory effect in the mouth including cooling or warming effects.
- Such ingredients include, without limitation, menthol, menthyl acetate, menthyl lactate, camphor, eucalyptus oil, eucalyptol, anethole, eugenol, cassia, oxanone, Irisone ® , propenyl guaiethol, thymol, linalool, benzaldehyde, cinnamaldehyde, N-ethyl-p-menthan-3-carboxamine, N,2,3-trimethyl-2-isopropylbutanamide, 3-(1-menthoxy)-propane-1,2-diol, cinnamaldehyde glycerol acetal (CGA), and menthone glycerol acetal (MGA).
- One or more flavorants are optionally present in a total amount of about 0.01-5.0 wt% (e.g., about 0.1-2.5 wt%), for example,
- An oral care composition in certain embodiments may comprise at least one whitening agent and/or colorant.
- a suitable whitening agent is a peroxide compound such as any of those disclosed in U.S. Patent No. 8540971 .
- Suitable colorants herein include pigments, dyes, lakes and agents imparting a particular luster or reflectivity such as pearling agents, for example.
- Specific examples of colorants useful herein include talc; mica; magnesium carbonate; calcium carbonate; magnesium silicate; magnesium aluminum silicate; silica; titanium dioxide; zinc oxide; red, yellow, brown and black iron oxides; ferric ammonium ferrocyanide; manganese violet; ultramarine; titaniated mica; and bismuth oxychloride.
- One or more colorants are optionally present in a total amount of about 0.001-20 wt% (e.g., about 0.01-10 wt% or about 0.1-5.0 wt%), for example, in the disclosed oral care composition.
- Additional components that can optionally be included in an oral composition herein include one or more enzymes (above), vitamins, and anti-adhesion agents, for example.
- vitamins useful herein include vitamin C, vitamin E, vitamin B5, and folic acid.
- suitable anti-adhesion agents include solbrol, ficin, and quorum-sensing inhibitors.
- the disclosed invention also concerns a method for increasing the viscosity of an aqueous composition.
- This method comprises contacting one or more poly alpha-1 ,3-glucan ether compounds disclosed herein with the aqueous composition. This step results in increasing the viscosity of the aqueous composition.
- the poly alpha-1 ,3-glucan ether compound(s) used in this method can be represented by the structure:
- n can be at least 6, and each R can independently be an H or an organic group.
- the poly alpha-1,3-glucan ether compound has a degree of substitution of about 0.05 to about 3.0. Any hydrocolloid and aqueous solution disclosed herein can be produced using this method.
- the contacting step can be performed by mixing or dissolving a poly alpha-1,3-glucan ether compound(s) disclosed herein in the aqueous composition by any means known in the art.
- mixing or dissolving can be performed manually or with a machine (e.g., industrial mixer or blender, orbital shaker, stir plate, homogenizer, sonicator, bead mill).
- Mixing or dissolving can comprise a homogenization step in certain embodiments.
- Homogenization (as well as any other type of mixing) can be performed for about 5 to 60, 5 to 30, 10 to 60, 10 to 30, 5 to 15, or 10 to 15 seconds (or any integer between 5 and 60 seconds), or longer periods of time as necessary to mix a poly alpha-1,3-glucan ether compound with the aqueous composition.
- a homogenizer can be used at about 5000 to 30000 rpm, 10000 to 30000 rpm, 15000 to 30000 rpm, 15000 to 25000 rpm, or 20000 rpm (or any integer between 5000 and 30000 rpm), for example.
- Hydrocolloids and aqueous solutions disclosed herein prepared using a homogenization step can be termed as homogenized hydrocolloids and aqueous solutions.
- Non-limiting examples of fabric types herein include fabrics made of (i) cellulosic fibers such as cotton (e.g., broadcloth, canvas, chambray, chenille, chintz, corduroy, cretonne, damask, denim, flannel, gingham, jacquard, knit, matelassé, oxford, percale, poplin, plissé, sateen, seersucker, sheers, terry cloth, twill, velvet), rayon (e.g., viscose, modal, lyocell), linen, and Tencel ® ; (ii) proteinaceous fibers such as silk, wool and related mammalian fibers; (iii) synthetic fibers such as polyester, acrylic, nylon, and the like; (iv) long vegetable fibers from jute, flax, ramie, coir, kapok, sisal, henequen, abaca, hemp and sunn; and (v) any combination
- an anionic poly alpha-1,3-glucan ether compound e.g., carboxyalkyl poly alpha-1,3-glucan such as carboxymethyl poly alpha-1,3-glucan
- material comprising natural fiber (e.g. cotton) and/or synthetic fiber (e.g., polyester).
- Such adsorption of an anionic poly alpha-1,3-glucan ether compound can be at least about 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, 120%, 140%, 160%, 180%, or 200% greater than the adsorption of the same glucan ether to a cotton fabric (e.g., cretonne), for example.
- Adsorption of a poly alpha-1,3-glucan ether compound to a fabric herein can be measured following the methodology disclosed in the below Examples, for example.
- adsorption can be measured using a colorimetric technique (e.g., Dubois et al., 1956, Anal. Chem. 28:350-356 ; Zemlji ⁇ et al., 2006, Lenzinger Berichte 85:68-76) or any other method known in the art.
- a treatment method in certain embodiments can be considered an oral care method or dental care method, for example.
- Conditions (e.g., time, temperature) for contacting an oral surface with an aqueous composition herein should be suitable for the intended purpose of making such contact.
- Other surfaces that can be contacted in a treatment method also include a surface of the integumentary system such as skin, hair or nails.
- certain embodiments of the disclosed invention concern material (e.g., fabric) that comprises a poly alpha-1,3-glucan ether compound herein.
- material e.g., fabric
- Such material can be produced following a material treatment method as disclosed, for example.
- a material may comprise a glucan ether compound in certain embodiments if the compound is adsorbed to, or otherwise in contact with, the surface of the material.
- An aqueous composition used in a treatment method herein can be any aqueous composition disclosed herein, such as in the above embodiments or in the below Examples.
- the poly alpha-1,3-glucan ether component(s) of an aqueous composition can be any as disclosed herein.
- aqueous compositions include detergents (e.g., laundry detergent or dish detergent) and water-containing dentifrices such as toothpaste.
- Poly alpha-1,3-glucan ether compounds useful for preparing the hydrocolloids and aqueous solutions of the present invention can be prepared as disclosed in U.S. Patent Appl. Publ. No. 2014/0179913 , and as disclosed herein, for example.
- alkali hydroxides can be used, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, and/or tetraethylammonium hydroxide.
- concentration of alkali hydroxide in a preparation with poly alpha-1,3-glucan and a solvent can be from about 1-70 wt%, 5-50 wt%, 10-50 wt%, 10-40 wt%, or 10-30 wt% (or any integer between 1 and 70 wt%).
- the concentration of alkali hydroxide such as sodium hydroxide can be at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 wt%.
- An alkali hydroxide used to prepare alkaline conditions may be in a completely aqueous solution or an aqueous solution comprising one or more water-soluble organic solvents such as ethanol or isopropanol.
- an alkali hydroxide can be added as a solid to provide alkaline conditions.
- organic solvents that can optionally be included when preparing the reaction include alcohols, acetone, dioxane, isopropanol and toluene, for example; none of these solvents dissolve poly alpha-1,3-glucan. Toluene or isopropanol can be used in certain embodiments. An organic solvent can be added before or after addition of alkali hydroxide.
- the concentration of an organic solvent (e.g., isopropanol or toluene) in a preparation comprising poly alpha-1,3-glucan and an alkali hydroxide can be at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 wt% (or any integer between 10 and 90 wt%).
- an organic solvent e.g., isopropanol or toluene
- solvents that can dissolve poly alpha-1,3-glucan can be used when preparing the reaction.
- solvents include, but are not limited to, lithium chloride(LiCI)/N,N-dimethyl-acetamide (DMAc), SO 2 /diethylamine (DEA)/dimethyl sulfoxide (DMSO), LiCI/1,3-dimethy-2-imidazolidinone (DMI), N,N-dimethylformamide (DMF)/N 2 O 4 , DMSO/tetrabutyl-ammonium fluoride trihydrate (TBAF), N-methylmorpholine-N-oxide (NMMO), Ni(tren)(OH) 2 [tren1 ⁇ 4tris(2-aminoethyl)amine] aqueous solutions and melts of LiClO 4 ⁇ 3H 2 O, NaOH/urea aqueous solutions, aqueous sodium hydroxide, aqueous potassium hydroxide, formic acid, and ionic liquid
- Poly alpha-1,3-glucan can be contacted with a solvent and one or more alkali hydroxides by mixing. Such mixing can be performed during or after adding these components with each other. Mixing can be performed by manual mixing, mixing using an overhead mixer, using a magnetic stir bar, or shaking, for example. In certain embodiments, poly alpha-1,3-glucan can first be mixed in water or an aqueous solution before it is mixed with a solvent and/or alkali hydroxide.
- the resulting composition can optionally be maintained at ambient temperature for up to 14 days.
- ambient temperature refers to a temperature between about 15-30 °C or 20-25 °C (or any integer between 15 and 30 °C).
- the composition can be heated with or without reflux at a temperature from about 30 °C to about 150 °C (or any integer between 30 and 150 °C) for up to about 48 hours.
- the composition in certain embodiments can be heated at about 55 °C for about 30 minutes or 60 minutes.
- composition obtained from mixing a poly alpha-1,3-glucan, solvent, and one or more alkali hydroxides with each other can be heated at about 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, or 60 °C for about 30-90 minutes.
- the resulting composition can optionally be filtered (with or without applying a temperature treatment step).
- filtration can be performed using a funnel, centrifuge, press filter, or any other method and/or equipment known in the art that allows removal of liquids from solids. Though filtration would remove much of the alkali hydroxide, the filtered poly alpha-1,3-glucan would remain alkaline (i.e., mercerized poly alpha-1,3-glucan), thereby providing alkaline conditions.
- An etherification agent comprising an organic group can be contacted with poly alpha-1,3-glucan in a reaction under alkaline conditions in a method herein of producing poly alpha-1,3-glucan ether compounds.
- an etherification agent can be added to a composition prepared by contacting poly alpha-1,3-glucan, solvent, and one or more alkali hydroxides with each other as described above.
- an etherification agent can be included when preparing the alkaline conditions (e.g., an etherification agent can be mixed with poly alpha-1,3-glucan and solvent before mixing with alkali hydroxide).
- An etherification agent herein refers to an agent that can be used to etherify one or more hydroxyl groups of the glucose units of poly alpha-1,3-glucan with an organic group as defined above. Examples of such organic groups include alkyl groups, hydroxy alkyl groups, and carboxy alkyl groups. One or more etherification agents may be used in the reaction.
- Etherification agents suitable for preparing an alkyl poly alpha-1,3-glucan ether compound include, for example, dialkyl sulfates, dialkyl carbonates, alkyl halides (e.g., alkyl chloride), iodoalkanes, alkyl triflates (alkyl trifluoromethanesulfonates) and alkyl fluorosulfonates.
- alkyl halides e.g., alkyl chloride
- iodoalkanes alkyl triflates (alkyl trifluoromethanesulfonates) and alkyl fluorosulfonates.
- examples of etherification agents for producing methyl poly alpha-1,3-glucan ethers include dimethyl sulfate, dimethyl carbonate, methyl chloride, iodomethane, methyl triflate and methyl fluorosulfonate.
- Examples of etherification agents for producing ethyl poly alpha-1,3-glucan ethers include diethyl sulfate, diethyl carbonate, ethyl chloride, iodoethane, ethyl triflate and ethyl fluorosulfonate.
- Examples of etherification agents for producing propyl poly alpha-1,3-glucan ethers include dipropyl sulfate, dipropyl carbonate, propyl chloride, iodopropane, propyl triflate and propyl fluorosulfonate.
- Examples of etherification agents for producing butyl poly alpha-1,3-glucan ethers include dibutyl sulfate, dibutyl carbonate, butyl chloride, iodobutane and butyl triflate.
- Etherification agents suitable for preparing a hydroxyalkyl poly alpha-1,3-glucan ether compound include, for example, alkylene oxides such as ethylene oxide, propylene oxide (e.g., 1,2-propylene oxide), butylene oxide (e.g., 1,2-butylene oxide; 2,3-butylene oxide; 1,4-butylene oxide), or combinations thereof.
- propylene oxide can be used as an etherification agent for preparing hydroxypropyl poly alpha-1,3-glucan
- ethylene oxide can be used as an etherification agent for preparing hydroxyethyl poly alpha-1,3-glucan.
- hydroxyalkyl halides e.g., hydroxyalkyl chloride
- hydroxyalkyl halides can be used as etherification agents for preparing hydroxyalkyl poly alpha-1,3-glucan.
- hydroxyalkyl halides include hydroxyethyl halide, hydroxypropyl halide (e.g., 2-hydroxypropyl chloride, 3-hydroxypropyl chloride) and hydroxybutyl halide.
- alkylene chlorohydrins can be used as etherification agents for preparing hydroxyalkyl poly alpha-1,3-glucan.
- Alkylene chlorohydrins that can be used include, but are not limited to, ethylene chlorohydrin, propylene chlorohydrin, butylene chlorohydrin, or combinations of these.
- Etherification agents suitable for preparing a dihydroxyalkyl poly alpha-1,3-glucan ether compound include dihydroxyalkyl halides (e.g., dihydroxyalkyl chloride) such as dihydroxyethyl halide, dihydroxypropyl halide (e.g., 2,3-dihydroxypropyl chloride [i.e., 3-chloro-1,2-propanediol]), or dihydroxybutyl halide, for example.
- dihydroxyalkyl halides e.g., dihydroxyalkyl chloride
- dihydroxypropyl halide e.g., 2,3-dihydroxypropyl chloride [i.e., 3-chloro-1,2-propanediol]
- dihydroxybutyl halide e.g., 2,3-dihydroxypropyl chloride
- 2,3-dihydroxypropyl chloride can be used to prepare dihydroxypropyl poly alpha-1,3-glucan, for
- Etherification agents suitable for preparing a carboxyalkyl poly alpha-1,3-glucan ether compound may include haloalkylates (e.g., chloroalkylate).
- haloalkylates include haloacetate (e.g., chloroacetate), 3-halopropionate (e.g., 3-chloropropionate) and 4-halobutyrate (e.g., 4-chlorobutyrate).
- chloroacetate dichloroacetate
- sodium chloroacetate or chloroacetic acid can be used as an etherification agent to prepare carboxymethyl poly alpha-1,3-glucan.
- two or more different etherification agents When producing a poly alpha-1,3-glucan ether compound with two or more different organic groups, two or more different etherification agents would be used, accordingly.
- both an alkylene oxide and an alkyl chloride could be used as etherification agents to produce an alkyl hydroxyalkyl poly alpha-1,3-glucan ether.
- Any of the etherification agents disclosed herein may therefore be combined to produce poly alpha-1,3-glucan ether compounds with two or more different organic groups.
- Such two or more etherification agents may be used in the reaction at the same time, or may be used sequentially in the reaction. When used sequentially, any of the temperature-treatment (e.g., heating) steps disclosed below may optionally be used between each addition.
- the amount of etherification agent to be contacted with poly alpha-1,3-glucan in a reaction under alkaline conditions can be determined based on the degree of substitution required in the poly alpha-1,3-glucan ether compound being produced.
- the amount of ether substitution groups on each monomeric unit in poly alpha-1,3-glucan ether compounds produced herein can be determined using nuclear magnetic resonance (NMR) spectroscopy.
- the molar substitution (MS) value for poly alpha-1,3-glucan has no upper limit.
- an etherification agent can be used in a quantity of at least about 0.05 mole per mole of poly alpha-1,3-glucan. There is no upper limit to the quantity of etherification agent that can be used.
- Reactions for producing poly alpha-1,3-glucan ether compounds herein can optionally be carried out in a pressure vessel such as a Parr reactor, an autoclave, a shaker tube or any other pressure vessel well known in the art.
- a shaker tube is used to perform the reaction in certain embodiments.
- a reaction herein can optionally be heated following the step of contacting poly alpha-1,3-glucan with an etherification agent under alkaline conditions.
- the reaction temperatures and time of applying such temperatures can be varied within wide limits.
- a reaction can optionally be maintained at ambient temperature for up to 14 days.
- a reaction can be heated, with or without reflux, between about 25 °C to about 200 °C (or any integer between 25 and 200 °C).
- Reaction time can be varied correspondingly: more time at a low temperature and less time at a high temperature.
- a reaction in certain embodiments of producing hydroxypropyl poly alpha-1,3-glucan, can be heated to about 75 °C for about 3 hours.
- a reaction for preparing hydroxyethyl poly alpha-1,3-glucan can be heated to about 60 °C for about 6 hours, for example.
- a reaction for preparing a hydroxyalkyl poly alpha-1,3-glucan herein can optionally be heated to about 55 °C to about 80 °C (or any integer between 55 and 80 °C) for about 2 hours to about 7 hours, for example.
- a reaction in certain embodiments of producing carboxymethyl poly alpha-1,3-glucan, can be heated to about 55 °C for about 3 hours.
- a reaction for preparing a carboxyalkyl poly alpha-1,3-glucan herein can be heated to about 50 °C to about 60 °C (or any integer between 50 and 60 °C) for about 2 hours to about 5 hours, for example.
- poly alpha-1,3 glucan is added to an alkali hydroxide solution (e.g., tetraethylammonium hydroxide) (e.g., about 20 wt% solution) to a final concentration or mass contribution of poly alpha-1,3 glucan of about 4, 5, 6, 7, or 8 wt% (e.g., ⁇ 6.5 wt%).
- alkali hydroxide solution e.g., tetraethylammonium hydroxide
- an appropriate etherification agent e.g., a dihydroxyalkyl chloride such as 2,3-dihydroxypropyl chloride
- a final concentration of about 7, 8, 9, 10, or 11 wt% e.g., ⁇ 9.5 wt%.
- the resulting reaction can be held at about 50 °C to about 60 °C (or any integer between 50 and 60 °C, e.g., 55 °C) for about 1.5-2.5 hours (e.g. about 2 hours), for example, before neutralizing the reaction.
- Water-soluble dihydroxyalkyl poly alpha-1,3-glucan can be produced by employing these steps.
- a reaction herein can be maintained under an inert gas, with or without heating.
- inert gas refers to a gas which does not undergo chemical reactions under a set of given conditions, such as those disclosed for preparing a reaction herein.
- a poly alpha-1,3-glucan ether compound produced in a reaction herein can optionally be washed one or more times with a liquid that does not readily dissolve the compound.
- poly alpha-1,3-glucan ether can be washed with water, alcohol, acetone, aromatics, or any combination of these, depending on the solubility of the ether compound therein (where lack of solubility is desirable for washing).
- a solvent comprising an organic solvent such as alcohol is preferred for washing a poly alpha-1,3-glucan ether.
- a poly alpha-1,3-glucan ether product can be washed one or more times with an aqueous solution containing methanol or ethanol, for example.
- 70-95 wt% ethanol can be used to wash the product.
- a poly alpha-1,3-glucan ether product can be washed with a methanol:acetone (e.g., 60:40) solution in another embodiment.
- Hot water (about 95-100 °C) can be used in certain embodiments, such as for washing alkyl poly alpha-1,3-glucan ethers (e.g., ethyl poly alpha-1,3-glucan) and alkyl hydroxyalkyl poly alpha-1,3-glucan ethers (e.g., ethyl hydroxyethyl poly alpha-1,3-glucan).
- a poly alpha-1,3-glucan ether produced in the disclosed reaction can be isolated. This step can be performed before or after neutralization and/or washing steps using a funnel, centrifuge, press filter, or any other method or equipment known in the art that allows removal of liquids from solids. For example, a Buchner funnel may be used to isolate a poly alpha-1,3-glucan ether product.
- An isolated poly alpha-1,3-glucan ether product can be dried using any method known in the art, such as vacuum drying, air drying, or freeze drying.
- poly alpha-1,3-glucan has less than about 50%, 40%, 30%, 20%, 10%, 5%, 4%, 3%, 2%, 1%, or 0% (or any integer value between 0% and 50%) of glycosidic linkages that are not alpha-1,3.
- Poly alpha-1,3-glucan used to prepare poly alpha-1,3-glucan ether compounds herein is preferably linear/unbranched.
- poly alpha-1,3-glucan has no branch points or less than about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1% branch points as a percent of the glycosidic linkages in the polymer.
- branch points include alpha-1,6 branch points.
- the M n or M w of poly alpha-1,3-glucan used to prepare poly alpha-1,3-glucan ether compounds herein may be at least about 1000 to about 600000.
- M n or M w can be at least about 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, 15000, 20000, 25000, 30000, 35000, 40000, 45000, 50000, 75000, 100000, 150000, 200000, 250000, 300000, 350000, 400000, 450000, 500000, 550000, or 600000 (or any integer between 2000 and 600000), for example.
- Poly alpha-1,3-glucan used for preparing poly alpha-1,3-glucan ether compounds herein can be enzymatically produced from sucrose using one or more glucosyltransferase (gtf) enzymes.
- the poly alpha-1,3-glucan product of this enzymatic reaction can be purified before using it to prepare an ether using the disclosed process.
- a poly alpha-1,3-glucan product of a gtf reaction can be used with little or no processing for preparing poly alpha-1,3-glucan ether compounds.
- a gtf enzymatic reaction can include, in addition to poly alpha-1,3-glucan itself, various components such as sucrose, one or more gtf enzymes, glucose, fructose, leucrose, buffer, FermaSure ® , soluble oligosaccharides, oligosaccharide primers, bacterial enzyme extract components, borates, sodium hydroxide, hydrochloric acid, cell lysate, proteins and/or nucleic acids.
- the components of a gtf enzymatic reaction can include, in addition to poly alpha-1,3-glucan itself, sucrose, one or more gtf enzymes, glucose, and fructose, for example.
- the components of a gtf enzymatic reaction can include, in addition to poly alpha-1,3-glucan itself, sucrose, one or more gtf enzymes, glucose, fructose, leucrose and soluble oligosaccharides (and optionally bacterial enzyme extract components).
- poly alpha-1,3-glucan when in a slurry as disclosed herein, has not been purified or washed.
- a slurry represents a gtf enzymatic reaction that is complete or for which an observable amount of poly alpha-1,3-glucan has been produced, which forms a solid since it is insoluble in the aqueous reaction milieu (has pH of 5-7, for example).
- a poly alpha-1,3-glucan slurry can be prepared by setting up a gtf reaction as disclosed in U.S. Patent No. 7,000,000 or U.S. Patent Appl. Publ. Nos. 2013/0244288 and 2013/0244287 , for example.
- a poly alpha-1,3-glucan slurry can be entered, for example, into a reaction for producing a carboxyalkyl poly alpha-1,3-glucan such as carboxymethyl poly alpha-1,3-glucan.
- a wet cake of poly alpha-1,3-glucan can be used directly in any of the above processes for producing a poly alpha-1,3-glucan ether compound disclosed herein.
- a "wet cake of poly alpha-1,3-glucan” as used herein refers to poly alpha-1,3-glucan that has been separated (e.g., filtered) from a slurry and washed with water or an aqueous solution.
- a wet cake can be washed at least 1, 2, 3, 4, 5, or more times, for example.
- the poly alpha-1,3-glucan is not dried when preparing a wet cake.
- a wet cake is termed as "wet” given the retention of water by the washed poly alpha-1,3-glucan.
- a crosslinking agent is next dissolved in the poly alpha-1,3-glucan ether solution or mixture.
- concentration of the crosslinking agent in the resulting solution can be about 0.2 to 20 wt%, or about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, or 20 wt%.
- Poly alpha-1,3-glucan was prepared using a gtfJ enzyme preparation as described in U.S. Patent Appl. Publ. No. 2013/0244288 .
- This Example describes producing the glucan ether derivative, hydroxypropyl poly alpha-1,3-glucan.
- This Example describes producing the glucan ether derivative, hydroxyethyl poly alpha-1,3-glucan.
- the solids were filtered using a Buchner funnel with 35-micrometer filter paper. The solids were then washed in a beaker by adding a methanol:acetone (60:40 v/v) mixture and stirring with a stir bar for 20 minutes. The methanol:acetone mixture was then filtered away from the solids. This washing step was repeated two times. The solids, which had a slightly brown/beige color, were dried in a vacuum oven with a nitrogen bleed. The hydroxyethyl poly alpha-1,3-glucan product was soluble in a 10% NaOH solution. The MS of the dried product was reported by NMR to be 0.72.
- This Example describes producing the glucan ether derivative, ethyl poly alpha-1,3-glucan.
- Poly alpha-1,3-glucan is added to a shaker tube, after which sodium hydroxide (1-70% solution) and ethyl chloride are added to provide a reaction.
- the reaction is heated to 25-200 °C and held at that temperature for 1-48 hours before the reaction is neutralized with acetic acid.
- the solid thus formed is collected by vacuum filtration and washed, dried under a vacuum at 20-25 °C, and analyzed by NMR and SEC to determine the molecular weight and degree of substitution (DoS) of the ethyl poly alpha-1,3-glucan.
- DoS molecular weight and degree of substitution
- glucan ether derivative ethyl poly alpha-1,3-glucan
- This Example describes producing the glucan ether derivative, ethyl hydroxyethyl poly alpha-1,3-glucan.
- Poly alpha-1,3-glucan is added to a shaker tube, after which sodium hydroxide (1-70% solution) is added. Then, ethyl chloride is added followed by an ethylene oxide/ethyl chloride mixture to provide a reaction. The reaction is slowly heated to 25-200 °C and held at that temperature for 1-48 hours before being neutralized with acetic acid. The solid thus formed is collected by vacuum filtration and washed with hot water, dried under a vacuum at 20-70 °C, and analyzed by NMR and SEC to determine the molecular weight and DoS of the ethyl hydroxyethyl poly alpha-1,3-glucan.
- the glucan ether derivative ethyl hydroxyethyl poly alpha-1,3-glucan
- This Example describes producing the glucan ether derivative, methyl poly alpha-1,3-glucan.
- the resulting methyl poly alpha-1,3-glucan solid was filtered and neutralized with 20 mL 90% acetic acid, followed by three 200-mL ethanol washes. NMR analysis was performed, indicating that the DoS of the methyl poly alpha-1,3-glucan product was 1.2.
- Table 1 provides a list of DoS measurements for various samples of methyl poly alpha-1,3-glucan prepared using methods having certain modifications compared to the above method (refer to Table 1).
- the mercerization step alkali treatment of poly alpha-1,3-glucan prior to addition of methylating reagent
- Table 1 was conducted for 1 hour, as above.
- glucan ether derivative methyl poly alpha-1,3-glucan
- This Example describes producing water-soluble methyl poly alpha-1,3-glucan.
- a solution of the methyl poly alpha-1,3-glucan product in water was prepared by dissolving 0.2 g of the product in 9.8 g water and mixing at room temperature. A clear solution was formed thereby indicating that the methyl poly alpha-1,3-glucan product was water-soluble.
- water-soluble methyl poly alpha-1,3-glucan was prepared and isolated.
- This Example describes producing the glucan ether derivative, hydroxyalkyl methyl poly alpha-1,3-glucan.
- Poly alpha-1,3-glucan is added to a vessel, after which sodium hydroxide (5-70% solution) is added. This preparation is stirred for 0.5-8 hours. Then, methyl chloride is added to the vessel to provide a reaction, which is then heated to 30-100 °C for up to 14 days. An alkylene oxide (e.g., ethylene oxide, propylene oxide, butylene oxide, etc.) is then added to the reaction while controlling the temperature. The reaction is heated to 25-100 °C for up to 14 days before being neutralized with acid. The solid product thus formed is filtered, washed and dried.
- sodium hydroxide 5-70% solution
- methyl chloride is added to the vessel to provide a reaction, which is then heated to 30-100 °C for up to 14 days.
- An alkylene oxide e.g., ethylene oxide, propylene oxide, butylene oxide, etc.
- the reaction is heated to 25-100 °C for up to 14 days before being neutralized with acid.
- the glucan ether derivative hydroxyalkyl methyl poly alpha-1,3-glucan
- hydroxyalkyl methyl poly alpha-1,3-glucan is prepared and isolated.
- this derivative include hydroxyethyl methyl poly alpha-1,3-glucan, hydroxypropyl methyl poly alpha-1,3-glucan, and hydroxybutyl methyl poly alpha-1,3-glucan.
- This Example describes producing the glucan ether derivative, carboxymethyl hydroxyethyl poly alpha-1,3-glucan.
- the glucan ether derivative carboxymethyl hydroxyethyl poly alpha-1,3-glucan, is prepared and isolated.
- This Example describes producing the glucan ether derivative, sodium carboxymethyl hydroxyethyl poly alpha-1,3-glucan.
- Poly alpha-1,3-glucan is added to an aliquot of an alcohol such as isopropanol in a 400-mL capacity shaker tube, after which sodium hydroxide (1-70% solution) is added. This preparation is stirred for up to 48 hours. Then, sodium monochloroacetate is added to provide a reaction, which is then heated to 25-100 °C for up to 14 days. Ethylene oxide is then added to the reaction, which is then heated to 25-100 °C for up to 14 days before being neutralized with acid (e.g., acetic, sulfuric, nitric, hydrochloric, etc.). The solid product thus formed is collected by vacuum filtration, washed and dried.
- an alcohol such as isopropanol
- sodium hydroxide (1-70% solution
- This preparation is stirred for up to 48 hours.
- sodium monochloroacetate is added to provide a reaction, which is then heated to 25-100 °C for up to 14 days.
- Ethylene oxide is
- the glucan ether derivative sodium carboxymethyl hydroxyethyl poly alpha-1,3-glucan, is prepared and isolated.
- This Example describes producing the glucan ether derivative, carboxymethyl hydroxypropyl poly alpha-1,3-glucan.
- glucan ether derivative carboxymethyl hydroxypropyl poly alpha-1,3-glucan
- This Example describes producing the glucan ether derivative, sodium carboxymethyl hydroxypropyl poly alpha-1,3-glucan.
- Table 2 provides a list of DoS measurements for various samples of sodium carboxymethyl poly alpha-1,3-glucan prepared using the above method.
- the poly alpha-1,3-glucan starting material had various molecular weights (Table 2).
- Table 2 DoS of Sodium Carboxymethyl Poly Alpha-1,3-Glucan Prepared from Poly Alpha-1,3-Glucan CMG Sample Designation M w of poly alpha-1,3-glucan starting material DoS 1A (35) 140287 0.5 1B (36) 140287 0.9 1C (39) 140287 1 1D (44) 88445 0.7 1E (47) 278858 0.7 1F (58) 248006 1G (67) 236854 0.5 1H (72) 236854 0.9 1I (-41) 200000 0.5 1J (-39) 168584 0.5
- a second solution of 2 wt% CMG (1G, Table 2) was prepared as in Example 16 using the homogenization method. The solution was divided into two aliquots. One aliquot was adjusted to pH 3.0 using citric acid and the second aliquot was adjusted to pH 12 using sodium hydroxide.
- This Example describes the effect of sucrose on the viscosity of CMG in solution.
- KNaCMG samples were subjected to various shear rates using a Brookfield III+ Rheometer equipped with a recirculating bath to control temperature (20 °C) and a YULA15-E(Z) spindle.
- the shear rate was increased using a gradient program which increased from 0.01-250 rpm and the shear rate was increased by 7.36 (1/s) every 20 seconds.
- the results of this experiment are listed in Table 12.
- LiNaCMG samples were subjected to various shear rates using a Brookfield III+ Rheometer equipped with a recirculating bath to control temperature (20 °C) and a YULA15-E(Z) spindle.
- the shear rate was increased using a gradient program which increased from 0.01-250 rpm and the shear rate was increased by 7.36 (1/s) every 20 seconds.
- the results of this experiment are listed in Table 14.
- LiNaCMG when dissolved in an aqueous solution not only modifies the viscosity of the solution, but also the rheological properties of the solution. LiNaCMG can therefore be added to an aqueous liquid to modify its rheological profile.
- LiCMG lithium carboxymethyl poly alpha-1,3-glucan
- This Example describes producing the glucan ether derivative, methyl poly alpha-1,3-glucan (MG). This Example is in addition to Examples 5 and 6, which describe producing MG.
- the reaction was held at temperature for 17 hours and then charged with an additional 20 g of methyl chloride and held at temperature for 17 hours. After cooling, the reaction was neutralized with 90% acetic acid.
- the solid from this reaction was collected by vacuum filtration, washed with methanol three times, dried under vacuum at 20-25 °C, and analyzed by NMR to determine DoS. The solid material obtained was identified as MG with a DoS of 1.75.
- the solid was collected by vacuum filtration and washed with methanol:acetone (60:40) five times, dried under vacuum at 20-25 °C, and analyzed by NMR to determine DoS.
- the solid material obtained was identified as MG with a DoS of 1.8. This MG was denoted as Sample 1.
- the solid was collected by vacuum filtration and washed with methanol:acetone (60:40) five times, dried under vacuum at 20-25 °C, and analyzed by NMR to determine DoS.
- the solid material obtained was identified as MG. This MG was denoted as Sample 2.
- This Example describes the effect of shear rate on the viscosity of MG. It is shown that MG exhibits shear thinning behavior. Thus, addition of MG to a liquid can modify the rheological behavior of the liquid.
- MG samples were subjected to 10-250 rpm shear rates using a Brookfield DV III+ Rheometer equipped with a recirculating bath to control temperature (20 °C) and an SC4-21 Thermosel ® spindle or ULA (ultra low adapter) spindle and adapter set.
- the shear rate was increased using a gradient program which increased from 10-250 rpm.
- the shear rate was increased by 7.35 (1/s) every 20 seconds for the ULA spindle and adapter, and by 4.9 (1/s) every 20 seconds for the SC4-21 spindle.
- Table 15 The results of this experiment are listed in Table 15.
- MG when dissolved in an aqueous solution not only modifies the viscosity of the solution, but also the rheological properties of the solution. MG can therefore be added to an aqueous liquid to modify its rheological profile.
- glucan ether derivative ethyl poly alpha-1,3-glucan
- the EG solutions were subjected to various shear rates using a Brookfield DV III+ Rheometer equipped with a recirculating bath to control temperature (20 °C) and an SC4-21 Thermosel ® spindle or ULA spindle and adapter set.
- the shear rate was increased using a gradient program which increased from 10-250 rpm.
- the shear rate was increased by 7.35 (1/s) every 20 seconds for the ULA spindle and adapter, and by 4.9 (1/s) every 20 seconds for the SC4-21 spindle.
- Table 16 The results of this experiment are listed in Table 16.
- EG when dissolved in an aqueous solution not only modifies the viscosity of the solution, but also the rheological properties of the solution. EG can therefore be added to an aqueous liquid to modify its rheological profile.
- This Example describes producing the glucan ether derivative, hydroxypropyl poly alpha-1,3-glucan (HPG). This Example is in addition to Example 1, which describes a method for producing HPG.
- HPG hydroxypropyl poly alpha-1,3-glucan
- This Example describes producing a dihydroxyalkyl ether derivative of poly alpha-1,3-glucan. Specifically, dihydroxypropyl poly alpha-1,3-glucan was produced.
- This Example describes producing dihydroxypropyl poly alpha-1,3-glucan. This Example is in addition to Example 34, which also describes producing this glucan ether derivative.
- 3-chloro-1,2-propanediol (16 g) was then added to provide a reaction (containing ⁇ 9.5 wt% 3-chloro-1,2-propanediol), which was held at 55 °C for 2 hours before being neutralized with acetic acid. After neutralization, an excess of isopropanol was added to precipitate a solid. The solid thus formed was collected by vacuum filtration and washed with ethanol (95%) four times, and dried under vacuum at 20-25 °C. The solid material obtained was identified as dihydroxypropyl poly alpha-1,3-glucan that was water soluble, and having a degree of substitution of 0.6.
- This Example describes the effect of shear rate on the viscosity of dihydroxypropyl poly alpha-1,3-glucan. It is shown that this glucan ether exhibits shear thinning behavior. Thus, addition of dihydroxypropyl poly alpha-1,3-glucan to a liquid can modify the rheological behavior of the liquid.
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Claims (15)
- Hydrokolloid oder wässrige Lösung, umfassend eine Poly-alpha-1,3-glucanether-Verbindung, die durch die folgende Struktur wiedergegeben wird:(i) n mindestens 6 ist,(ii) R jeweils unabhängig für H oder eine organische Gruppe steht,(iii) die Verbindung einen Substitutionsgrad von etwa 0,05 bis etwa 3,0 aufweist,(iv) das Hydrokolloid bzw. die wässrige Lösung eine Viskosität von mindestens etwa 10 Centipoise aufweist und(v) die Poly-alpha-1,3-glucanether-Verbindung vernetzt ist.
- Hydrokolloid oder wässrige Lösung nach Anspruch 1, wobei mindestens eine organische Gruppe aus der Gruppe bestehend aus Alkyl, Hydroxyalkyl und Carboxyalkyl ausgewählt ist.
- Hydrokolloid oder wässrige Lösung nach Anspruch 2, wobei mindestens eine organische Gruppe aus der Gruppe bestehend aus Methyl, Ethyl, Hydroxypropyl, Dihydroxypropyl und Hydroxyethyl ausgewählt ist.
- Hydrokolloid oder wässrige Lösung nach Anspruch 2, wobei mindestens eine organische Gruppe Carboxymethyl ist.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-4, wobei die Verbindung eine Art von organischer Gruppe enthält.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-4, wobei die Verbindung zwei oder mehr Arten von organischer Gruppe enthält.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-6, wobei der Substitutionsgrad etwa 0,2 bis etwa 2,0 beträgt.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-7, wobei der pH-Wert des Hydrokolloids bzw. der wässrigen Lösung zwischen etwa 4,0 bis etwa 8,0 liegt.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-8, wobei das Hydrokolloid bzw. die wässrige Lösung in Form eines pharmazeutischen Produkts, Lebensmittelprodukts oder technischen Produkts vorliegt.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-8, wobei das Hydrokolloid bzw. die wässrige Lösung in Form eines Haushaltsprodukts vorliegt.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-8, wobei das Hydrokolloid bzw. die wässrige Lösung in Form eines Körperpflegeprodukts vorliegt.
- Hydrokolloid oder wässrige Lösung nach Anspruch 11, wobei es sich bei dem Körperpflegeprodukt um eine Hautpflegezusammensetzung handelt.
- Hydrokolloid oder wässrige Lösung nach Anspruch 11, wobei es sich bei dem Körperpflegeprodukt um eine kosmetische Zusammensetzung handelt.
- Hydrokolloid oder wässrige Lösung nach Anspruch 11, wobei es sich bei dem Körperpflegeprodukt um eine Lotion oder eine Salbe handelt.
- Hydrokolloid oder wässrige Lösung nach einem der Ansprüche 1-8, wobei das Hydrokolloid bzw. die wässrige Lösung in Form einer Geschirrspülmittelzusammensetzung oder Waschmittelzusammensetzung vorliegt.
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CA2932498C (en) | 2023-03-14 |
US20220306770A1 (en) | 2022-09-29 |
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EP4163305A1 (de) | 2023-04-12 |
KR20160099629A (ko) | 2016-08-22 |
US10005850B2 (en) | 2018-06-26 |
AU2014366222A1 (en) | 2016-06-09 |
WO2015095046A1 (en) | 2015-06-25 |
JP6598778B2 (ja) | 2019-10-30 |
CN106255707B (zh) | 2019-06-18 |
US20160304629A1 (en) | 2016-10-20 |
CN106255707A (zh) | 2016-12-21 |
BR112016013684A2 (pt) | 2017-08-08 |
EP3083704A1 (de) | 2016-10-26 |
US10865254B2 (en) | 2020-12-15 |
US20180291122A1 (en) | 2018-10-11 |
US20210261692A1 (en) | 2021-08-26 |
CA2932498A1 (en) | 2015-06-25 |
MX2016007759A (es) | 2016-08-19 |
JP2017509718A (ja) | 2017-04-06 |
AU2014366222B2 (en) | 2018-07-19 |
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